Catalytic reduction of reducing a carbon-carbon unsaturated bond, that is, a carbon-carbon triple bond (C≡C) or a carbon-carbon double bond (C═C), into a carbon-carbon saturated bond (C—C) achieves high production efficiency, uses hydrogen as a clean reagent, gives a few waste products, and thus is widely used in industries. For example, in the production of margarine, a nickel salt supported on purified diatomaceous earth is dry-reduced, dispersed in a hardened oil, and solidified, and the resulting nickel catalyst is used for the catalytic reduction. In the production of agrochemicals or drugs, a palladium catalyst such as Lindlar catalyst is used for the catalytic reduction.
However, when a compound having a halogen atom in the molecule is subjected to catalytic reduction using a nickel boride catalyst without a catalyst poison or using a palladium catalyst, dehalogenation simultaneously occurs unfortunately (G. Chelucci et al., ChemistrySelect, 2016, 1, 3699-3704; B. Nand et al., Can. J. Chem., 2008, 86, 1052-1054; and R. P. Sharma et al., Tetrahedron Letters, 1985, 26 (38), 4657-4660).
Accordingly, there have been reported, for example, a method of using a platinum catalyst such as platinum oxide (Marcel Apparu et al., Bull. Soc. Chim. Fr., 1988, 1, 118-124), a method of using a Raney nickel catalyst (JP 2011-207901A), and a method of using a nickel boride catalyst together with a catalyst poison for reducing the activity (Jean-Luc Parrain et al., Synlett, 2001, 4, 553-556; and Takashi Miyachi et al., J. Chem. Ecol., 2015, 41, 1-8).